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Swain is probably one of the biggest contradictions with casters: His ultimate wants you in the middle of the fight as opposed to skirting the outside. Tack on the fact that he's a MAJOR mana drain you can easily fail with him. Here's how i run him.
Start with Amp tome and a health pot. Since you have Clarity you can skip the typical mana regen item for now until you get your farming on. Swain is great in the mid but i still prefer him to sidelane with a support or tank, especially Rammus or Shen for their taunt.
EARLY GAME RULES
Rule 1: DONT WASTE MANA : This means dont use Decrepify to last hit minions. Once you get Nevermore you have a better farming tool, which gets better with the second point. You alos cant stay in ult mode too long, you drain really fast after 5 seconds.
Rule 2: DONT BE STUPID : Swain has a great amount of damage but until he gets to level 6 you wont be able to head in like Annie would. Play it safe until 6 and you'll be able to kill anyone.
Rule 4: REMEMBER THE SEQUENCE: Torment makes all of your other moves and r-clicks hit 20% harder, so always open with it. If you can time it right throw Nevermore then Torment, if you are lucky or skilled enough Torment will trigger before the root happens. Follow up the opener with Flock and Decrepify. Once you finish Deathfire you'll do that BEFORE Flock or Lazerbird.
So the sequence is;
3. Deathfire Grasp
4. Ravenous Flock
That should take down pretty much any squish and a good chunk of a decent tank. Be careful about retaliation though, Swain is still a caster and has little to no defense so being focused is bad.
: Pretty much the ticket for Swain. Once Torment is on you hit the with this, dealing the 30% or their health PLUS and additional 20% of that, ending up at 36% and thats BEFORE you start building up your AP. With 400+ AP you hit them for 44%, which in turn is cracked up to 53% with Torment going. THATS OVER HALF OF THEIR HEALTH FROM JUST 2 MOVES!
: Like i've stated, Swain is a major mana pig, so Chalice combined with his passive allows you to stay at a comfortable amount of mana until mid-late game. I usually sell this off later to pick up another AP item, usually Lich Bane.
: This is a decent item on any caster who needs to be slightly tanky (Prime example, MORGANA). Picking up Catalyst early makes it easier to stay in lane and spam and when you convert it into Rod you only improve as you go.
: Rylai's makes you INCREDIBLY annoying, since each time the flock hits them the slow is refreshed. Tack on the health and ap boost and its a perfect addition to Swain.
: Again, a duh item. Huge AP with a cute defensive measure. It can even be used while you are IN ult mode, giving you 2 seconds of free life steal!
Boots are always situational, but for the most part if you are doing well go withand if you need help against CC go with.
assumes the best case scenario all the time, so i can't advocate it since you will never be flawless all the time. If you wanna try it out get it in place of Rod, but again, i prefer guarantees over potential.
is a great addition as well, especially if you get Lich Bane. It also adds another gun to the sequence and can used while Deathfire is on cooldown. Throw in the spell vamp AND life steal and you shold be sitting pretty.
FINAL NOTE: Realize that this is just a guide, substitute and supplement as the game dictates or whatever suites you. Summoner spells and runes are only slight edges to give you advantage, but ultimately its up to YOU as the summoner to pilot Swain as best as you can.
Happy hunting, and tell me about the MURDERS!